Thiourea → HCID 58075094, compound

Participants

Reaction Steps

Ethyl 3-(5-chloropyrazin-2-yl)-3-oxopropanoate (Intermediate 45, 2.0 g, 8.77 mM) was dissolved in ethyl acetate (30 mL), to this amberlyst resin (2.0 g) and N-iodosuccinamide (2.1 g, 9.64 mM) were added and stirred for 1 h at room temperature. The resin was filtered and the filtrate was concentrated under reduced pressure to afford crude compound, which was dissolved in methanol (25 mL). Thiourea (0.99 g, 13.15 mM) was added to the reaction mixture and the reaction mixture was heated to reflux for 2 h. The methanol was concentrated under reduced pressure and the resulting residue was partitioned between sodium bicarbonate solution (50 mL) and extracted with ethyl acetate (50 mL). The organic layers were combined and dried over anhydrous sodium sulphate, filtered, concentrated under reduced pressure to obtain crude compound which was purified by flash column chromatography (gradient up to 50% of ethyl acetate/pet ether) to afford 500 mg (20.06%) of ethyl 2-amino-4-(5-chloropyrazin-2-yl)-1,3-thiazole-5-carboxylate off-white solid.

Provenance & Evidence